In this episode of Inside the Workflow, I'm thrilled to welcome Jay Nathan, the CEO of Balboa Solutions. Jay is a tech executive and entrepreneur with over 20 years of experience in driving customer success and growth in the SaaS industry. Notably, he has conducted over 350 interviews through his own podcast, offering a wealth of insights into the tech landscape.

In This Episode, We Discuss:

1. Entrepreneurial Beginnings: Jay shares how his early experiences in his parents' retail business shaped his approach to customer experience and quality standards.

2. Building Wealth through Ownership: Insights into Jay's journey of understanding wealth building through ownership and equity in businesses.

3. Product Development Philosophy: Jay's take on the concept of Minimum Viable Product (MVP) and the importance of testing market viability before full-scale product development.

4. Impact of AI on Business: Discussion on how AI is transforming business operations and the cost dynamics of product development.

5. Hiring and Team Building: Jay outlines his approach to hiring, emphasizing the importance of self-awareness, completing hard tasks, and the power of team unanimity in recruitment decisions.

Listeners will gain valuable perspectives on entrepreneurship, the strategic importance of ownership, and the evolving role of AI in tech businesses. Jay's insights into team building and career advice for young professionals are particularly enlightening.

Key Topics Covered:
[00:00] Introduction and Jay Nathan’s Background – Overview of Jay's career and podcasting experience.
[05:00] Entrepreneurial Influences – Jay discusses his early experiences in his family's retail business.
[10:00] Building Wealth through Business Ownership – Insights into the benefits of owning a stake in a business.
[15:00] MVP and Product Development – Jay’s perspective on launching products and testing market viability.
[20:00] AI's Role in Business – Examining how AI is reducing costs and reshaping business operations.
[25:00] Hiring Philosophy and Team Dynamics – Jay shares his approach to hiring and building effective teams.
[30:00] Career Advice for Young Professionals – Guidance on choosing the right first job and building a professional network.
[35:00] Closing Thoughts – Summary of key insights and reflections on the discussion.

💬 Comment below with your thoughts on entrepreneurship and the evolving role of AI.
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In this episode of Inside the Workflow, I'm thrilled to welcome Matt Bond, the Director of Customer Support at Algolia. With over 13 years in customer support, Matt has been instrumental in ensuring great customer outcomes and experiences. He started his career in customer service at a young age and has evolved through various technical roles, ultimately finding a perfect blend of customer interaction and technical expertise in his current role.

In This Episode, We Discuss:

1. Career Beginnings: Matt shares his journey from starting work at 13, studying environmental science, and gradually moving into technical roles, leading to his current position.

2. Handling High-Pressure Environments: Insights into managing stress and the importance of empathy in customer support.

3. Exercise and Mental Well-being: Matt emphasizes the importance of exercise, such as running, to maintain mental health and balance in high-stress situations.

4. Building Side Projects for Skill Enhancement: The value of pursuing side projects, like Matt's multiplayer game, to stay creative and learn new technologies.

5. Team Growth and Culture: Strategies for maintaining a strong team culture while scaling from five to twenty-three members and the importance of hiring the right fit.

Listeners will gain valuable insights into customer support dynamics, stress management, and the significance of team culture from Matt's extensive experience and thoughtful approaches.

Key Topics Covered:
[00:00] Introduction to Matt Bond and his career journey
[05:00] The impact of early customer service roles on career development
[10:00] Managing stress and the importance of exercise
[15:00] Building side projects and their role in skill enhancement
[20:00] Strategies for maintaining team culture and growth
[25:00] The role of AI in customer support and future prospects
[30:00] Listening to customers to build a great product
[35:00] Advice for those starting a career in customer-facing roles

💬 Comment below with your thoughts on the evolving role of AI in customer support. 🔔 Subscribe for future episodes!

In this episode of Inside the Workflow, I'm thrilled to welcome Fernando Duarte, the Director of Customer Success. With over 15 years of experience in customer-facing roles, Fernando is passionate about problem-solving and making customers the hero of their own stories. Not only has he built successful support teams across various companies, but he also brings a unique perspective from his love of organizing chaos through building complex Lego sets with his children.

In This Episode, We Discuss:

1. Building and Leading Successful Teams: Fernando shares insights on developing a team while running a business and maintaining low turnover with only one resignation in 16 years.

2. The Power of Empathy in Customer Support: Learn how empathy and active listening can transform customer interactions and foster long-lasting relationships.

3. The Role of AI in Customer Support: Discover how AI is not replacing jobs but augmenting them, allowing support agents to focus on relational interactions rather than transactional ones.

4. The Finite vs. Infinite Game in Business: Fernando discusses the importance of viewing customer interactions as part of an ongoing relationship rather than a one-time transaction.

5. The Evolution of Products and Customer Experience: Explore the need for products to be intuitive from the user's perspective and the value of customer feedback in product development.

Listeners will gain valuable insights into building effective customer support teams, leveraging AI technology, and enhancing customer experiences by understanding their perspectives. Fernando's approach to leadership and his emphasis on empathy provide a refreshing take on what it means to truly support customers.

💬 Comment below with your thoughts on customer experience and leadership strategies.

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In this episode of Inside the Workflow, Scott welcomes Nick Francis, Co-founder and CEO of Help Scout, for a deep, thoughtful conversation on entrepreneurship, customer support, product vision, and doing hard things—both in business and life.

Nick shares the 14-year journey of Help Scout, from its early days as a simple shared inbox tool to its transformation into a mission-driven customer support platform with a new pricing model designed for the AI era. He opens up about founding the company with close friends, the influence of hospitality on product design, building remote-first culture with intention, and why he’s obsessed with solving the customer support problem.

In This Episode, We Discuss:
 • The founding story of Help Scout & TechStars beginnings in Boston
 • Why great customer experiences are at the core of their product
 • Lessons from hospitality and brand building
 • Adopting a remote-first culture and maintaining team connection
 • How AI is transforming customer support—and how Help Scout is adapting

Whether you’re a founder, product builder, or support leader, this episode is packed with wisdom on building a durable business while staying true to your values.

Subscribe for more conversations with tech leaders who are reshaping the way we work.

In this episode, we sit down with Nicholas Thompson, CEO of The Atlantic and former Editor-in-Chief of Wired, to explore his path from student newspaper founder to leading one of the most influential media organizations in the world. With a deep understanding of journalism, tech innovation, and business leadership, Nicholas shares his thoughts on editorial independence, AI’s role in publishing, and building resilient teams in a fast-changing media landscape.

From running newsrooms to navigating the future of AI-driven journalism, this conversation is full of thought-provoking takeaways. Nicholas also opens up about what keeps him grounded, the importance of trust in leadership, and why great content always comes first—no matter the business model.

What You’ll Learn in This Episode: 

• The Evolution of Modern Journalism – How Nicholas’s early experiences shaped his leadership at The Atlantic.
•  Business vs. Editorial – Why a clear line between content and revenue is key to maintaining trust.
•  AI & the Newsroom – The promise and perils of artificial intelligence in journalism.
•  Leadership Style – How Nicholas fosters a culture of open debate, autonomy, and values-driven decision-making.
•  Career Advice – Why mentorship, ambition, and meaningful work matter in shaping a successful path.

Key Topics Covered:
 [00:00] Introduction & Nicholas’s Background – From student journalism to the CEO seat
 [05:00] Lessons from The Thinker – Early insights into editorial debate and business strategy
 [10:00] Building Strong Cultures – How to manage rival teams and competing business goals
 [15:00] Trust in Journalism – Why editorial independence is non-negotiable at The Atlantic
 [20:00] Embracing AI – How Nicholas uses AI in his daily life and what it means for journalism
 [25:00] The Future of Media – Competing with TikTok, evolving revenue models, and building resilience
 [30:00] Career Reflections – Advice for aspiring journalists and early-career professionals

Whether you're in media, leadership, or just fascinated by the intersection of journalism and technology, this episode offers powerful insights from one of the most thoughtful voices in the industry.

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 💬 Comment below with your thoughts on media, leadership, and the role of AI.

In this episode, we sit down with Dan O’Leary, Sr. Director of Strategic Partnerships at Box, to explore his journey from building SaaS partnerships at Meta to leading strategic growth initiatives at Box. With deep expertise in partner ecosystems, AI-driven collaboration, and enterprise SaaS, Dan shares valuable insights on leadership, scaling businesses, and the evolving role of AI in workflow automation.

From navigating competitive SaaS markets to fostering strong partnerships that drive customer success, this conversation is packed with actionable takeaways. Dan also shares his perspective on balancing work and life, the importance of communication in leadership, and why partnerships are more than just a growth strategy—they’re a way to deliver real customer value.

What You’ll Learn in This Episode:

🚀 Leadership & Team Building – How Dan fosters strong teams through clear communication and transparency.
 📈 Scaling Partnerships – Why strategic partnerships are key to SaaS growth and how to make them successful.
 🤖 AI in Enterprise Collaboration – How AI is reshaping workflows and driving productivity.
 🔄 Adapting to Change – Lessons from returning to Box and evolving with the industry.
 💡 Future of SaaS & Content AI – What’s next for AI-driven collaboration and partner ecosystems.

Key Topics Covered:

[00:00] Introduction & Dan’s Background – From Meta to Box and the evolution of SaaS partnerships.
 [05:00] Building Enterprise Software at a Consumer Tech Company – Lessons from launching Workplace at Meta.
 [10:00] The Role of Partnerships in SaaS – Why partnerships are more than just a sales channel.
 [15:00] AI & The Future of Work – How AI is improving collaboration and decision-making.
 [20:00] Leadership & Communication – Why great leaders focus on authenticity and clarity.
 [25:00] Balancing Work & Life – Dan’s perspective on prioritization and making time for what matters.
 [30:00] What’s Next in SaaS & Partnerships – Predictions for the future of collaboration tools and AI.

Whether you're a SaaS founder, enterprise leader, or curious about the future of AI-driven workflows, this episode is full of insights on leadership, partnerships, and innovation.

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 ✅ Enjoyed this episode? Like & share!
 💬 Comment below with your thoughts on AI, partnerships, and leadership.

In this episode, we sit down with Gil Lara, Chief Creative Officer and co-founder at Sprout Social, to discuss his nearly 15-year journey with the leading social media management platform. From his early days in street art and event design to building a creative culture at Sprout, Gil shares the evolution of his career and the pivotal moments that shaped him as a designer and leader. With insights on the changing landscape of design, embracing AI, and navigating the tension between creativity and business, this conversation is packed with valuable takeaways for anyone passionate about design and innovation.

Key Topics Covered:

0:00 - 5:00 – Introducing Gil Lara: Gil’s creative background, his move to Chicago to join Sprout Social’s founding team, and his early experiences with graffiti and event design.

5:00 - 10:00 – Finding Design Inspiration in Unusual Places: Gil shares how everyday objects, like shower controls, can spark creative ideas and the importance of observing the world around you.

10:00 - 15:00 – From Street Art to the Corporate World: How Gil transitioned from graffiti and print design to shaping digital experiences and software at Sprout Social.

15:00 - 20:00 – Building a Creative Culture at Sprout: The early days at Sprout, working on the social inbox, and how design has influenced the company’s evolution.

20:00 - 25:00 – Customer Feedback as a Design Tool: Why listening to customers and integrating their feedback is crucial, and how it can lead to innovative features.

25:00 - 30:00 – Balancing Innovation with Business Needs: Navigating the demands of building a social media management platform while staying true to the creative vision.

30:00 - 35:00 – The Role of AI in Social Media Management: How AI is transforming Sprout Social’s platform and the potential it has to revolutionize customer engagement.

35:00 - 40:00 – The Future of Design Leadership: Gil’s thoughts on passing the torch, embracing change, and preparing for his next chapter after stepping down from his role.

40:00 - 45:00 – Advice for Young Designers: Gil reflects on his career, shares lessons learned, and offers advice on how to advocate for design’s impact within an organization.

45:00 - 50:00 – The Power of Video and Storytelling: The importance of video in conveying a brand’s message and creating memorable experiences for customers and employees alike.

50:00 - 55:00 – Looking Ahead: Gil’s thoughts on the future of Sprout Social, his personal plans, and the exciting opportunities in the ever-evolving world of design and technology.

Key Takeaways:

• The Value of Design Thinking: Gil emphasizes the need for designers to go beyond aesthetics and partner early in the development process to create meaningful user experiences.
• Feedback as Fuel for Innovation: Leveraging customer insights and using them as a tool for continuous improvement.
• Navigating Healthy Tension: The importance of balancing different perspectives and embracing the creative friction that drives better outcomes.
• AI as a Game-Changer: How artificial intelligence is poised to transform the way businesses manage social media and engage with audiences.
• Evolving as a Leader: Gil reflects on his decision to step down, the significance of building a resilient team, and the excitement of pursuing new ventures.

Notable Quotes:

1. "If you're not defining what design is at your organization, someone else will define it for you."
2. "Healthy tension is a part of building something great."
3. "Ther

In this episode, we sit down with Philippe Mesritz, a Fractional Chief Customer Officer and former General Manager at Community Brands, known for transforming SaaS organizations and driving customer retention. Philippe shares his journey from web design and system administration to leading customer experience teams and improving Net Promoter Scores (NPS) by 40 points.

From building customer-centric teams to navigating the evolving role of AI in CX, Philippe’s insights are packed with actionable takeaways. He also shares his philosophy on transparency, vision, and adaptability in leadership, as well as the importance of balancing work and life while maintaining high performance.

What You’ll Learn in This Episode:

🚀 Leadership & Team Building – How Philippe fosters transparency, clarity, and vision to create high-performing teams.
 📈 Customer Success & Retention – Lessons from improving NPS and building long-term customer relationships.
 🤖 AI in Customer Experience – How AI is transforming CX, and why a human touch still matters.
 🔄 Adapting to Change – The role of resilience and continuous learning in career growth.
 💡 Future of CX & SaaS – How technology, customer insights, and evolving business models are shaping the future.

Key Topics Covered:

[00:00] Introduction & Philippe’s Background – From early tech roles to leading customer success.
 [05:00] Customer Experience in Unexpected Places – Lessons from SaaS to manufacturing.
 [10:00] Firing a Customer: The Right Way to Say No – Why sometimes the best CX decision is letting a customer go.
 [15:00] Building High-Performing Teams – The power of transparency, clarity, and vision in leadership.
 [20:00] Remote Work & Global Teams – Strategies for effective communication and engagement.
 [25:00] AI & The Future of Customer Experience – Why AI matters, but human relationships will always be key.
 [30:00] Career Growth & Leadership – Philippe’s advice on navigating a dynamic career path.

Whether you're a CX leader, SaaS founder, or someone passionate about customer success, this episode is packed with insights on leadership, AI, and the future of customer experience.

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 💬 Comment below with your thoughts on AI, leadership, and customer success.

In this episode of Inside the Workflow, we sit down with Ashley Smith, GP and Founder of Vermillion Cliffs Ventures. With a track record of driving growth at Twilio, GitLab, and GitHub, Ashley has now turned her focus to investing in early-stage technical founders. We explore her journey from startup operator to venture capitalist, her leadership approach, and what she looks for in founders building the next generation of developer-focused companies.

From her early career answering support calls at Twilio to leading go-to-market strategies for some of the biggest developer tools, Ashley shares invaluable lessons on building strong teams, navigating competition, and the evolving role of AI in software development.

What You’ll Learn in This Episode:

• Building High-Performing Teams – The key traits Ashley looks for in founders and early hires.
• Founder-Led Growth – Why technical founders must embrace go-to-market strategies.
• AI & Developer Tools – The latest trends in AI infrastructure and how startups can leverage automation.
• Scaling Startups – Lessons from Twilio, GitHub, and GitLab on rapid product adoption.
• The Future of Investing – Ashley’s approach to early-stage investing and what excites her in tech.

Key Topics Covered:

[00:00] Introduction & Ashley’s Background – From Twilio support to leading growth at top startups.
 [05:00] The Transition to Venture – Why Ashley founded Vermillion Cliffs Ventures.
 [10:00] Startup Team Building – What makes a great founding team and early hires.
 [15:00] AI’s Impact on Software Development – The shift from hype to real-world applications.
 [20:00] Founder-Led Sales – Why early-stage technical founders need to embrace GTM strategies.
 [25:00] The Future of Venture – How Ashley sees investing evolving in the next decade.
 [30:00] Leadership & Work-LifeBalance – Lessons from navigating startup intensity and VC life.

Whether you're a startup founder, investor, or AI enthusiast, this episode is packed with insights on building, scaling, and investing in the future of software and AI.

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 ✅ Like this episode if you enjoyed Ashley’s insights!
 💬 Comment below with your thoughts on venture capital, AI, and startup growth.

In this episode, we’re excited to welcome Todd Baylis, Chief Customer Officer at Bloomerang, to discuss his journey as an entrepreneur, his leadership philosophy, and the future of nonprofit technology. From founding Qgiv to driving innovation at Bloomerang, Todd shares how he’s transforming donor engagement and helping nonprofits build lasting relationships.

What You’ll Learn in This Episode:

• Todd’s leadership style and how he fosters a culture of innovation and customer-centricity.
• The evolution of nonprofit technology and how Bloomerang is streamlining donor engagement.
• Lessons from entrepreneurship—failing forward, adapting to challenges, and scaling a business.
• The role of automation and AI in freeing up time for nonprofits to focus on relationships.
• Todd’s approach to work-life balance as a leader and family man.

Key Topics Covered:

⏳ 0:00 – Introduction and Todd’s background in nonprofit technology.
 💡 5:00 – Leadership lessons: Building a strong culture in remote and hybrid teams.
 📈 10:00 – The biggest challenges nonprofits face in donor engagement and retention.
 🚀 15:00 – The future of nonprofit tech: AI, automation, and relationship-driven fundraising.
 🔍 20:00 – Todd’s entrepreneurial journey: Lessons from growing and selling a company.
 🏆 30:00 – The importance of resilience, adaptability, and continuous learning in leadership.

Todd’s insights into leadership, innovation, and customer success make this a must-listen episode. Tune in for valuable lessons on building a business, leading with purpose, and shaping the future of nonprofit technology.

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 👍 Like this episode if you enjoyed Todd’s insights!
 💬 Comment below with your thoughts on leadership, customer success, and nonprofit tech!